A description is given of the oxidation of 1,2,4,5- tetramethoxybenzene (TMB) with halogens to form the TMB cation radical and halide anions. The results obtained to date are outlined to show the existence of ion pair interactions in the esr spectra. Further necessary work to completely elucidate the nature and interactions of the species in solution are suggested. A possible mechanism for the oxidation is set forth and the suggestion is made that the system may provide a mode for other organic and biochemical oxidations. In this regard it is proposed to study the oxidation of benzo(a) pyrene (BP) with iodine in light of the results from the IMB-I2 system. BP is a chemical carcinogen and the free radicals formed from it are believed to be the proximate carcinogens. Antioxidants such as butylated hydroxytoluene have been shown to provide protection against the carcinogenic nature of BP. It is, therefore, also proposed to investigate on a molecular level the interactions between several antioxidants and aromatic cation radicals.